EP0885272A1 - Flüssigkristallzusammensetzung und flüssigkristallanzeigeelement - Google Patents

Flüssigkristallzusammensetzung und flüssigkristallanzeigeelement

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Publication number
EP0885272A1
EP0885272A1 EP97901795A EP97901795A EP0885272A1 EP 0885272 A1 EP0885272 A1 EP 0885272A1 EP 97901795 A EP97901795 A EP 97901795A EP 97901795 A EP97901795 A EP 97901795A EP 0885272 A1 EP0885272 A1 EP 0885272A1
Authority
EP
European Patent Office
Prior art keywords
denotes
liquid crystal
component
crystal composition
weight
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP97901795A
Other languages
English (en)
French (fr)
Other versions
EP0885272B1 (de
Inventor
Toshihiko Muraoka
Katsuyuki Murashiro
Fusayuki Takeshita
Tetsuya Matsushita
Etsuo Nakagawa
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
JNC Corp
Original Assignee
Chisso Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chisso Corp filed Critical Chisso Corp
Publication of EP0885272A1 publication Critical patent/EP0885272A1/de
Application granted granted Critical
Publication of EP0885272B1 publication Critical patent/EP0885272B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
    • C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
    • C09K19/46—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
    • C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
    • C09K2019/0451—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a CH3CH=CHCH2CH2- chain

Definitions

  • the present invention relates to a nematic liquid crystal composition containing at least one chiral additive arranged within a sealed cell formed of two substrates having transparent electrodes and a liquid crystal display element with use of the said liquid crystal composition.
  • the invention relates to a liquid crystal composition suitable for a super twist birefringence (STN) mode and a liquid crystal display element with use of the said liquid crystal composition.
  • STN super twist birefringence
  • the liquid crystal composition used for the liquid crystal display element of the said STN mode is required to have the following characteristics:
  • a voltage - transmittance characteristic (a sharpness) being sharp in order to increase a contrast of the liquid crystal display element
  • phase transition temperature (a transparent point) being high in order to decrease a change in coloring due to a
  • an object of the invention is to propose a liquid crystal composition which satisfies various characteristics required for the above- mentioned STN display mode and simultaneously has a superior voltage - transmittance characteristic (a sharpness) for corresponding to coloring and also a low viscosity for
  • a liquid crystal composition characterized in that at least one compound expressed by the general formulae I-a and I-b
  • R 1 denotes an alkyl group having from 1 to 10 carbon atom(s)
  • Z° denotes -COO- or -CH 2 CH 2 -
  • Z 1 denotes -CH 2 CH 2 -, -COO- or a single bond
  • Q 1 denotes H or F
  • Al denotes trans-1,4- cyclohexylene, 1,4-phenylene or 1,3-dioxane-2, 5-diyl
  • a 2 and A 3 denote each independently trans-1,4-cyclohexylene or 1,4- phenylene
  • p, q and m each independently denote 0 or 1.
  • a liquid crystal composition described in the above- mentioned item (1) characterized in that the first component is from 3 to 50% by weight, the second component is from 3 to 40% by weight and the third component is from 10 to 60% by weight, all based on the total weight of the liquid crystal composition.
  • B denotes trans-1,4-cyclohexylene, pyrimidine-2,5-diyl or 1,4-phenylene
  • C denotes trans-1,4- cyclohexylene or 1,4-phenylene
  • -CF CF- or a single bond.
  • R 6 denotes an alkyl group, an alkoxy group or an
  • D denotes trans-1,4-cyclohexylene or pyrimidine-2,5-diyl
  • E denotes trans- 1,4-cyclohexylene or 1,4-phenylene in which one H at a branched position may be optionally substituted with F
  • G denotes trans- 1,4-cyclohexylene or 1,4-phenylene
  • Z 3 denotes -CH 2 CH 2 - or a single bond
  • R 7 denotes an alkyl group having from 1 to 10 carbon atom(s)
  • R a denotes an alkyl group, an alkoxy group or an
  • alkoxymethyl group having from 1 to 10 carbon atom (s), and Q 2 denotes H or F.) is contained as the fourth component.
  • a liquid crystal composition described in the above- mentioned item (3) characterized in that the first component is from 3 to 50% by weight, the second component is from 3 to 40% by weight, the third component is from 10 to 60% by weight, and the fourth component is from 1 to 60% by weight, all based on the total weight of the liquid crystal composition.
  • a liquid crystal composition characterized in that at least one compound expressed by the general formulae I-a and I-b
  • Z° denotes -COO- or -CH 2 CH 2 -
  • Z 1 denotes -CH 2 CH 2 , -COO- or a single bond
  • Q 1 denotes H or F
  • a 1 denotes trans-1,4- cyclohexylene, 1,4-phenylene or 1,3-dioxane-2, 5-diyl
  • a 2 and A 3 denote each independently trans-1,4-cyclohexylene or 1,4- phenylene
  • p, q and m each independently denote 0 or 1.
  • B denotes trans-1,4-cyclohexylene, pyrimidine-2,5-diyl or 1, 4-phenylene
  • C denotes trans-1,4- cyclohexylene or 1,4-phenylene
  • R 6 denotes an alkyl group, an alkoxy group or an
  • D denotes trans-1, 4-cyclohexylene or pyrimidine-2, 5-diyl
  • E denotes trans- 1, 4-cyclohexylene or 1,4-phenylene in which one H at a branched position may be optionally substituted with F
  • G denotes trans- 1, 4-cyclohexylene or 1,4-phenylene
  • Z 3 denotes -CH 2 CH 2 - or a single bond
  • R 7 denotes an alkyl group having from 1 to 10 carbon atom(s)
  • R 8 denotes an alkyl group, an alkoxy group or an
  • alkoxymethyl group having from 1 to 10 carbon atom(s), and Q z denotes H or F.) is contained as the fourth component, and at least one or more than one compound (s) selected from the group consisting of compounds expressed by the general formulae VII and VIII
  • R 9 denotes an alkyl group having from 1 to 10 carbon atom (s), Q 3 denotes H or F, and k denotes 0 or 1)
  • R 10 denotes an alkyl group having from 1 to 10 carbon atom(s)
  • J denotes trans-1
  • Q 4 and Q 5 denote each independently H or F
  • Z 5 and Z 6 denote each independently -COO- or a single bond
  • h denotes 0, 1 or 2.
  • a liquid crystal composition described in the above- mentioned item (5) characterized in that the first component is from 3 to 50% by weight, the second component is from 3 to 40% by weight, the third component is from 10 to 60% by weight, the fourth component is from 1 to 60% by weight, and the fifth component is from 1 to 50% by weight, all based on the total weight of the liquid crystal composition.
  • a liquid crystal display element comprising a liquid crystal composition described in any of the above-mentioned items (1) to (6).
  • liquid crystal compounds constituting the liquid crystal compositions according to the invention are explained as follows.
  • These compounds are those with weak positive dielectric anisotropies and large refractive anisotropies ( ⁇ n) such as ⁇ n> 0.1, and they are used mainly for a purpose to enlarge a nematic range or for purposes to lower a viscosity and improve a sharpness.
  • R denotes an alkyl group.
  • R denotes an alkyl group.
  • III-c-5), (III-c-6), (III-c-7), (III-c-10) or (III-c-11) are preferably used.
  • These compounds for the third component are those with positive dielectric anisotropies of large values, and they are used mainly for a purpose to lower a threshold voltage and a purpose to improve a sharpness which is important as a STN characteristic.
  • Compounds expressed by the general formulae IV and V, Vl-a, VI-b are those with negative or weak positive dielectric anisotropies.
  • Compounds of the general formula IV are used mainly for purposes to lower a viscosity and/or to control ⁇ n.
  • compounds of the general formula V are used for a purpose to enlarge a nematic range such as raising of a
  • Vl-a and VI-b have very high transparent points. Thus, they are used for a purpose to enlarge a nematic range such as raising of a transparent point and/or for a purpose of ⁇ n control.
  • VIII-15 (VIII-16) or (VIII-18) are preferably used according to the invention.
  • Compounds expressed by the general formulae VII and VIII are those with positive dielectric anisotropies and they are used particularly for a purpose to lower a threshold voltage and a purpose to improve a temperature dependency. Furthermore, they are used for purposes of viscosity control, ⁇ n control, and nematic range enlargement such as raising of a transparent point.
  • An amount of the first component used according to the invention is preferably from 3 to 50% by weight based on the total weight of the liquid crystal composition. From 5 to 40% by weight is more preferable. If it being less than 3% by weight, effects of the subjective sharpness and high-speed responce are difficult to be obtained, and if it being above 50% by weight, the threshold voltage of the liquid crystal composition becomes high, which is not desirable.
  • An amount of the second component used is preferably from 3 to 40% by weight. From 4 to 35% by weight is more preferable. If it being less than 3% by weight, effects of the subjective sharpness and high-speed responce are difficult to be obtained, and if it being above 40% by weight, the threshold voltage of the liquid crystal composition becomes high, which is not desirable.
  • An amount of the third component used is preferably from 10 to 60% by weight. If it being less than 10% by weight, the threshold voltage of the liquid crystal composition becomes high, which is not desirable. If it being above 60% by weight, the viscosity of the liquid crystal composition becomes high, which is not desirable.
  • An amount of the fourth component used is preferably from 0 to 60% by weight. From 0 to 50% by weight is more preferable. If it being above 60% by weight, the threshold voltage of the liquid crystal composition becomes high, which is not desirable.
  • An amount of the fifth component used is preferably from 0 to 50% by weight. From 0 to 40% by weight is more preferable.
  • the liquid crystal composition according to the invention may contain another compounds for purposes of controlling a threshold voltage, a nematic range, ⁇ n, a dielectric anisotropy and a viscosity etc., within suitable ranges of amounts not damaging the objects of the invention.
  • a threshold voltage a nematic range, ⁇ n, a dielectric anisotropy and a viscosity etc.
  • R denotes an alkyl group having from 1 to 10 carbon atoms.
  • the liquid crystal composition according to the invention is prepared by any of the conventional processes. Generally, there may be used a process to dissolve various components each other at an elevated temperature. Furthermore, the liquid crystal materials of the invention are improved and optimized by means of suitable additives according to their intended applications. The said additives are well-known by the skilled men in the art and described in detail in literatures etc. Generally, a chiral dopant and so on are added in order to derive a spiral structure of liquid crystals and adjust a required twist angle for prevention of reversetwist.
  • liquid crystal composition to be used according to the invention can be used as a liquid crystal composition for a guest-host (GH) mode with addition of
  • bichromatic dyes such as merocyanine type, styryl type, azo type, azomethine type, azoxy type, quinophthalone type,
  • the composition can be used as a liquid crystal composition for a polymer disperse type liquid crystal display element (PNLCD), for example, NCAP made by microcapsulating nematic crystals or a polymer network liquid crystal display element (PNLCD) having three-dimensional network macromolecules made in liquid
  • PLCD polymer disperse type liquid crystal display element
  • NCAP made by microcapsulating nematic crystals
  • PLCD polymer network liquid crystal display element having three-dimensional network macromolecules made in liquid
  • composition can be used as a liquid crystal composition for a birefringence control (ECB) mode or a dinamic scattering (DS) mode.
  • EBC birefringence control
  • DS dinamic scattering
  • thickness d was selected in such a way that the product ⁇ n ⁇ d of a cell thickness d and a refractive anisotropy ⁇ n being about 0.85, and a chiral compound was added in such a way that a ratio d/p of a cell thickness d to a pitch p of a liquid crystal composition being about 0.5 and thereafter poured into a cell.
  • composition A was prepared from the following components:
  • a liquid crystal composition was prepared by mixing 85 parts by wight of the composition A in Comparative Example 1 and 15 parts by weight of a compounds having the following formula contained in the general formula (I):
  • V 10 /V 90 1.282.
  • T NI 100.0 ( °C).
  • V 10 /V 90 1.090.
  • V 10 /V 90 1.091.
  • V 10 /V 90 1.082.
  • CM-33 0.63 parts by weight of a chiral compound CM-33 was added to 100 parts by weight of this liquid crystal composition to prepare a composition, which was then poured into a 240 ° STN cell having a thickness of d-5.9 ⁇ m, and the cell was evaluated by means of an yellow mode.
  • V 10 /V 90 1.098.
  • V 10 /V 90 1.094.
  • a liquid crystal composition consisting of the following components was prepared:
  • V 10 /V 90 1.076.
  • a liquid crystal composition consisting of the following components was prepared:
  • V 10 /V 90 1.054.
  • a liquid crystal composition consisting of the following components was prepared:
  • V 10 /V 90 1.034.
  • a liquid crystal composition consisting of the following components was prepared:
  • V 10 /V 90 1.142.
  • a liquid crystal composition consisting of the following components was prepared:
  • V 10 /V 90 1.068.
  • the transparent point became high and the viscosity became low. Furthermore, the sharpness was more improved than the compositon in the Comparative Example 2.
  • a liquid crystal composition consisting of the following components was prepared:
  • V 10 /V 90 1.078.
  • a liquid crystal composition consisting of the following components was prepared:
  • V 10 /V 90 1.070.
  • a liquid crystal composition consisting of the following components was prepared:
  • a liquid crystal composition consisting of the following components was prepared:
  • T NI 75.8( °C)
  • V-T characteristic A voltage - transmittance characteristic
  • a liquid crystal composition consisting of the following components was prepared:
  • V-T characteristic A voltage - transmittance characteristic
  • a liquid crystal composition consisting of the following components was prepared:
  • a liquid crystal composition consisting of the following components was prepared:
  • a liquid crystal composition consisting of the following components was prepared:
  • V-T characteristic A voltage - transmittance characteristic
  • a liquid crystal composition consisting of the following components was prepared:
  • V-T characteristic A voltage - transmittance characteristic
  • a liquid crystal compsition which satisfies various characteristics required for a STN display mode and also which is superior in a voltage - transmittance characteristic (a sharpness) necessary for corresponding particularly to coloring, as well as a liquid crystal
  • composition with a low viscosity necessary for corresponding to a high-speed response can be proposed according to the

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  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Liquid Crystal Substances (AREA)
EP97901795A 1996-03-07 1997-01-31 Flüssigkristallzusammensetzung und flüssigkristallanzeigeelement Expired - Lifetime EP0885272B1 (de)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP80809/96 1996-03-07
JP08080996A JP3843480B2 (ja) 1996-03-07 1996-03-07 液晶組成物および液晶表示素子
JP8080996 1996-03-07
PCT/JP1997/000228 WO1997032943A1 (en) 1996-03-07 1997-01-31 Liquid crystal composition and liquid crystal display element

Publications (2)

Publication Number Publication Date
EP0885272A1 true EP0885272A1 (de) 1998-12-23
EP0885272B1 EP0885272B1 (de) 2002-07-03

Family

ID=13728806

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97901795A Expired - Lifetime EP0885272B1 (de) 1996-03-07 1997-01-31 Flüssigkristallzusammensetzung und flüssigkristallanzeigeelement

Country Status (6)

Country Link
US (1) US6207075B1 (de)
EP (1) EP0885272B1 (de)
JP (1) JP3843480B2 (de)
AU (1) AU1556897A (de)
DE (1) DE69713742T2 (de)
WO (1) WO1997032943A1 (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5062923B2 (ja) * 1998-12-07 2012-10-31 Ｊｎｃ株式会社 液晶組成物および液晶表示素子
DE10056323A1 (de) 1999-12-14 2001-06-21 Merck Patent Gmbh STN-Flüssigkristallanzeige
JP5100940B2 (ja) * 2000-12-04 2012-12-19 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング 液晶性媒体
DE102011118210A1 (de) * 2010-11-27 2012-05-31 Merck Patent Gmbh Flüssigkristallines Medium
JP5887713B2 (ja) * 2011-05-10 2016-03-16 Jnc株式会社 フルオロビニル誘導体、液晶組成物及び液晶表示素子
US8889035B2 (en) * 2012-08-17 2014-11-18 Jnc Corporation Liquid crystal composition and liquid crystal display device
CN103013533B (zh) * 2012-12-12 2014-12-17 深圳市华星光电技术有限公司 液晶组成物、液晶配向混合物及液晶面板
WO2017038616A1 (ja) * 2015-09-04 2017-03-09 Dic株式会社 ネマチック液晶組成物及びこれを用いた液晶表示素子

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Publication number Priority date Publication date Assignee Title
CA1336441C (en) 1987-12-28 1995-07-25 Manabu Uchida Liquid crystal composition
JPH01216967A (ja) * 1988-02-26 1989-08-30 Chisso Corp 液晶化合物
JP2657689B2 (ja) 1989-01-06 1997-09-24 チッソ株式会社 液晶性化合物
DE4018651B4 (de) * 1990-06-11 2005-12-22 Merck Patent Gmbh Flüssigkristallines Medium und seine Verwendung
DE4032579A1 (de) * 1990-10-13 1992-04-16 Merck Patent Gmbh Supertwist-fluessigkristallanzeige
DE59209827D1 (de) * 1991-02-12 2000-05-25 Merck Patent Gmbh Flüssigkristalline verbindungen
DE4217248B4 (de) * 1991-06-05 2005-06-16 Merck Patent Gmbh Vinylverbindungen
EP0559860B1 (de) * 1991-09-30 1996-02-14 F. Hoffmann-La Roche Ag Halovinylderivate
JP3605648B2 (ja) * 1994-12-12 2004-12-22 チッソ株式会社 液晶組成物および液晶表示素子
DE19707154A1 (de) * 1996-03-06 1997-09-11 Merck Patent Gmbh Difluorvinylether

Non-Patent Citations (1)

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Title
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Also Published As

Publication number Publication date
AU1556897A (en) 1997-09-22
DE69713742T2 (de) 2002-12-05
EP0885272B1 (de) 2002-07-03
US6207075B1 (en) 2001-03-27
JP3843480B2 (ja) 2006-11-08
DE69713742D1 (de) 2002-08-08
JPH09241644A (ja) 1997-09-16
WO1997032943A1 (en) 1997-09-12

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